“Are you coming in?” I ask as we stop outside the door to my cabin. “I was hoping to add up your points and see if you are due a prize.”
“I may be able to spare a moment for that,” he tells me with a smile as I locate the key-card and get the door to open for us.
“Okay, Evan. Please sit down for a moment while I add up your score for the night.” He smiles brightly, but does as I tell him and takes a seat on the edge of the bed while I sit on the chair at the desk and pick up a pencil and a sheet of paper.
“Let me see. Picked me up. Offered his arm. Seated me. Chose a very good wine with dinner.” I’m pretending to check items off a list as I go and Evan is giggling a bit at my antics. “Held hands on deck. Took us to a show. Walked me home. Evan, did I miss anything?”
“No, I don’t think so. How did I do?”
“Well, I think you’ve indeed done well enough to earn a prize.”
“Excellent. What did you have in mind?”
“Hmm… I think you get a place to sleep for the night,” I tell him indicating the bed he is sitting on.”
“Come here, you bloody idiot,” he tells me as he stifles another laugh and holds his hand out towards me.
I let him draw me towards him, but then push him over onto his back and straddle his waist, leaning forward to kiss him roughly. I start to rub myself against him as our kisses deepen, feeling the beginning of his arousal through the fabric of his pants.
“Can we be clinical for a moment, Adam?”
“Tested after I caught that bastard.”
“Oh. Yeah, tested about two months ago and I haven’t been with anyone since. I do have condoms.”
“I’d rather not as we’re both clean. Preferences?”
“I’m versatile, but prefer being top.”
“I prefer being bottom, so this might even work. There’s only one possible problem.” I tell him between more kisses and roaming hands.
“What problem?”
I allow my roaming hand to reach down and grasp his arousal through his trousers. “I’m not sure I can take this!”
“Hmm… But you’re willing to try?”
“Just get your clothes off and fuck me for God’s sake!” I moan as I start to unbutton my shirt. I have to stand while I get out of the rest of my clothes and give space for Evan to do the same. Once suitably naked I push him onto his back once more and drop to a crouch between his knees. Taking a firm grasp of his now fully erect cock with both hands, I begin to stroke him slowly as I run my tongue around the tip. As he drops his hands gently onto the back of my head, I take the whole of the head of him into my mouth and let my tongue explore the open part of his foreskin.
“Adam…” Evan moans as I continue to suck on his glans, easing the skin back with my lips. As he twitches, out of control, I relent and let him out of my mouth, just jerking gently with one hand while I stroke his balls with the other.
“Evan, fuck me!”
“Do you have any…”
“Lube, yeah. In the top drawer.”
I crawl up the bed beside him and reach into the drawer to find the small bottle and pop the lid. “We might be better with me kneeling for the first time. I’m really not sure you’ll fit.” I tell him as I hand him the bottle.
From my kneeling position I can sense Evan position himself behind me, but I’m still surprised when the tip of his tongue glides across my hole lightly before circling a few times and darting fleetingly. Within moments I feel a cold slippery finger at my entrance before Evan pushes his digit gently inside me and starts to move it slowly.
As a second finger joins the first, I grip my own shaft firmly with one hand and begin to stroke myself slowly. Evan’s fingers are moving easily, slipping in and out as he twists and turns them slightly inside me.
The fingers are withdrawn and Evan positions himself behind me. I feel a steady pressure on my entrance and then a sudden painful stretching as the huge head of his cock penetrates. “Ahh…” I manage between clenched teeth. “Slowly…”
Evan holds his position for a few moments then very slowly begins to push deeper inside. I can feel myself stretching to accommodate him with an exquisite slightly painful ripple of tingling nerve endings that only serve to increase the speed of my hand. The sensation as his girth slides over my prostate is almost overpowering.
“Okay Adam?” Evan whispers as he stops his inward motion.
“Start slow…”
Evan’s hands grasp my hips careful of my bruising and he draws back, more slowly and for more length than I ever thought possible before thrusting back deep into me. As he repeats this slow thrusting, I continue to slide my hand up and down my throbbing shaft, trying to match our rhythms.
What was initially so huge and painful is now intensely pleasurable as it plunges deep inside me and draws back repeatedly. As Evan increases his pace, I do as well, now pushing back slightly with each of his thrusts, almost unbelievably wanting him even deeper inside me.
As I sense myself approaching my climax, Evan starts to thrust quick and shallow, his rhythm beginning to break down as he also reaches the end. “Coming…” I pant with one final tight stroke of my hand. As my orgasm begins, the first spurts of semen bursting from me, Evan thrusts deep and moans in ecstasy as his own orgasm hits. His cock twitches and pulses deep inside me as he releases his load.
Evan falls forward to rest along my back, panting heavily as his spasms lessen and my own pulsing orgasm ends.
As he rolls off me to flop down onto his back on the mattress, I moan slightly as he slips from inside me, already starting to go soft. I lower myself down beside him and drape one arm across his belly, snuggling into his shoulder as he slides his arm under my neck.
We lie together for a few minutes as our breathing slowly normalises. Evan’s fingers are drawing little circles on my shoulder and mine are moving equally slowly around the edge of his navel.
“Is everything okay?” he asks me quietly.
“Yes, I think so. You really are huge, aren’t you?”
“Once I left school, and stopped getting teased about it, I never really gave it much thought. I know it’s a bit big, but it’s not huge.”
“Well, it sure felt huge. I thought I was going to split open!”
“I didn’t hurt you, did I?”
“Oh, no. It was a bit tight at first, but I seemed to get accustomed to it pretty quickly. It was wonderful. I might feel differently about it in the morning though.”
“I… Nobody ever…”
“What Evan?”
“Nobody ever took it all on their first attempt before. You were so hot, so tight, but it felt incredible.”
I can tell that I’m starting to feel a little sleepy. “Evan, are you staying tonight?”
Adam has just moved to a new apartment, just broken up with his boyfriend and just about had enough. When his Mum books a cruise for him to get away from it all and enjoy some photography time alone, he almost says no to the offer.
When she tells him it’s too late to get a refund, he reluctantly agrees to spend a week cruising the Scottish Islands. When he is asked if he minds sharing a table with another single guest at dinner, he meets Evan, an up-and-coming YouTube travel vlogger on a working holiday.
Well, there’s no harm in spending time with another guest for a week, is there?
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